President James Longstreet's decision to order the manumission of the Confederacy's slave population cost Featherston his job, which the ex-overseer deeply resented for the rest of his life. His married life seems to have been unhappy and marred by violent scenes.

He taught his son Jake some "overseer lore" such as how to detect when a black person was lying or concealing something, which the younger Featherston would later apply in dealings with Blacks during military service in the Great War. At the time of the war's outbreak, the elder Featherston and his wife were already dead.

In 1936, President Jake Featherston had a confrontation with General Jeb Stuart Jr. during which the general insulted the President's dead father and called him "white trash". This was the final trigger which led to Jake Featherston destroying Jeb Stuart's career and reputation, though he was inclined to take such an action anyway.